Methylamine → HCID 9937522, compound

HRID 1958285Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]([OH:29])[CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH:26]4[CH2:28][O:27]4)[CH2:21][CH2:20]3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[CH3:30][NH2:31]>>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:16][CH:17]([OH:29])[CH2:18][N:19]3[CH2:20][CH2:21][N:22]([CH2:25][CH:26]([OH:27])[CH2:28][NH:31][CH3:30])[CH2:23][CH2:24]3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

Participants

Reactant 2

HCID 6329Methylamine

HCID 17810496HCID 17810496, compound

Product 1

HCID 9937522HCID 9937522, compoundYield 90%

Procedure

To (±)-1-(3,6-dibromo-carbazol-9-yl)-3-(4-oxiranylmethyl-piperazin-1-yl)-propan-2-ol (0.110 g, 0.21 mmol) is added methyl amine (3 mL, 2M in MeOH). The resulting mixture was stirred for 16 hr at it Concentration in vacuo, flash chromatography on a 2×14 cm2 column of SiO2 using (ACN:(aqueous NH4OH-25%)) (5:1) as eluting solvent gives the title compound as a white foam in a 90% yield. M.p.: 65-75° C. Slow addition of HCl (1 mL, 1M in Et2O) into a solution of the above compound in DCM (2 mL) gives the hydrochloride salt of the title compound (0.39 g) as a white solid in a 35% yield.

Workup

washas eluting solvent

Sources & evidence

ORD record: ord-fec5cf32d4e04075a5714470ba43ffcc
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410110B2

Reaction notes

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